A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation

Organic Letters

Volumn 14, Issue 4, 2012, Pages 1138-1141

  Romney, David K ^a   Miller, Scott J ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; FLUORINE DERIVATIVE; KETONE; PEPTIDE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

CATALYSIS; EPOXY COMPOUNDS; FLUORINE COMPOUNDS; KETONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEPTIDES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84863410740     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3000712     Document Type: Article

References (27)

1. Adam, W.; Zhao, C.-G.; Saha-Möller, C. R.; Jakka, K. Oxidation of Organic Compounds by Dioxiranes; Wiley: Hoboken, NJ, 2009.
2. Wong, O.; Shi, Y. Chem. Rev. 2008, 108, 3958-3987
3. Wang, Z. X.; Tu, Y.; Frohn, M.; Zhang, J. R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224-11235
4. Curci, R.; D'Accolti, L.; Fusco, C. Acc. Chem. Res. 2006, 39, 1-9
5. Wender, P. A.; Hilinski, M. K.; Mayweg, A. V. W. Org. Lett. 2005, 7, 79-82
6. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175
7. Berkessel, A. Curr. Opin. Chem. Biol. 2003, 7, 409-419
8. Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495
9. Agarkov, A.; Greenfield, S.; Xie, D.; Pawlick, R.; Starkey, G.; Gilbertson, S. R. Biopolymers 2006, 84, 48-73
10. Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem.-Eur. J. 1998, 4, 1885-1889
11. Juliá, S.; Masana, J.; Vega, J. C. Angew. Chem., Int. Ed. 1980, 19, 929-931
12. Kelly, D. R.; Roberts, S. M. Biopolymers 2006, 84, 74-89
13. Berkessel, A.; Koch, B.; Toniolo, C.; Rainaldi, M.; Broxterman, Q. B.; Kaptein, B. Biopolymers 2006, 84, 90-96
14. Peris, G.; Jakobsche, C.; Miller, S. J. Am. Chem. Soc. 2007, 129, 8710-8711
15. Blank, J. T.; Miller, S. J. Biopolymers 2006, 84, 38-47
16. Jakobsche, C.; Peris, G.; Miller, S. Angew. Chem., Int. Ed. 2008, 47, 6707-6711
17. Hintermann, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 2093-2126
18. Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975-6985
19. Miller, S. J. Acc. Chem. Res. 2004, 37, 601-610
20. Shu, L.; Shi, Y. Tetrahedron Lett. 1999, 40, 8721-8724
21. Burke, C. P.; Shu, L.; Shi, Y. J. Org. Chem. 2007, 72, 6320-6323
22. Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860
23. Bach, R. D.; Andres, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207-7217
24. Berti, G.; Macchia, B.; Macchia, F.; Monti, L. J. Org. Chem. 1968, 33, 4045-4049
25. Bulman Page, P. C.; Buckley, B. R.; Blacker, A. J. Org. Lett. 2004, 6, 1543-1546
26. Witkop, B.; Foltz, C. M. J. Am. Chem. Soc. 1957, 79, 197-201
27. Fujisawa, T.; Takemura, I.; Ukaji, Y. Tetrahedron Lett. 1990, 31, 5479-5482